Anticonvulsant activity of thymoquinone and its structural analogues

Abstract

It has been widely reported that the crude oil of Nigella sativa L., Ranunculaceae, seeds and its major chemical component thymoquinone present anticonvulsant activity. These facts led us to verify the pharmacological potential of five structurally related para-benzoquinones on the pentylenotetrazol-induced seizures model, and establish the structural characteristics that influence the anticonvulsant activity of thymoquinone. The unsubstituted para-benzoquinone was the compound that exhibited the highest potency, while 2-methyl-p-benzoquinone was inactive. It was found that the presence of alkyl groups attached to the ring influence the pharmacological activity of the para-benzoquinones. In addition, the number, position, and size of these groups change the anticonvulsant potency of the compounds.

Differentiation of Nigella sativa seeds from four different origins and their bioactivity correlations based on NMR-metabolomics approach

“…These observations are consistent with the fact that the triterpenoid saponins and flavonoid glycoside are more soluble in aqueous methanol. The assignment of compounds were supported by comparison with the literature data [thymol and thymol-b-glucopyranoside (Ahmed and Jakupovic, 1990), thymoquinone (de Sousa et al, 2011), fatty acids (Knothe and Kenar, 2004), p-cymene (Schwarz and Ernst, 1996), cycloartenol (Mehta et al, 2009), sucrose, quercetin, and kaempferol (Maulidiani et al, 2012)]. Identification of thymol, thymoquinone, fatty acids, pcymene, thymol-b-glucopyranoside, and sucrose was also confirmed by 2D NMR data (HMBC and J resolved).…”

The Ameliorative Effect of Thymoquinone on Vincristine-Induced Peripheral Neuropathy in Mice by Modulating Cellular Oxidative Stress and Cytokine

“…Thymoquinone (TQ) from Nigella sativa is a bioactive compound that has been extensively studied for its many pharmacological actions, such as antioxidant, anti-inflammatory, cytoprotective, immunomodulatory, antineoplastic, antibacterial, antidiabetic, and analgesic effects [ 18 , 19 , 20 ]. In addition, TQ offers various beneficial effects which are pertinent to neurological disorders, including antiepileptic [ 21 ], antianxiety [ 22 ], antidepressant [ 23 ], antipsychotic, and the amelioration of memory impairment [ 24 ], and thus improves the quality of life in neuropathic patients. TQ treatment has shown an ameliorative effect on pain originating from neurodegeneration induced by mechanical injury to the spinal cord in rats [ 25 ].…”

The polymerization of carvacrol catalyzed by Mn-porphyrins: obtaining the desired product guided by the choice of solvent, oxidant, and catalyst

“…1–4 Thymoquinone (Scheme 1), a representative of this class and the main product from carvacrol oxidation, shows interesting properties such as antitumor, hepatoprotective and anticonvulsant properties, making it a sought-after substance. 1,5–7 Therefore, some studies on carvacrol's oxidation aiming to produce thymoquinone and other products (Scheme 1) were attempted. 4,8,9…”